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Think email is old news? Think again. Jessica Best helps us dive into why your first-party email list is marketing’s most powerful asset, how to troubleshoot falling open rates with the latest authentication protocols, and which automated sequences fuel growth – from lead nurtures to birthday campaigns. Perfect for small business owners and marketers eager to see real ROI from their inbox.
Email Marketing’s Hidden Superpowers (And Why Most Marketers Never Unlock Them)
Recently I was interviewing Jessica Best, owner and chief strategist of BetterAve, a consultancy focused on implementing email best practices for their clients. Jessica has over 15 years of experience helping clients drive revenue from customer data, and our chat focused on email marketing’s “superpowers”, including the fact that it’s one of the few platforms where you have ownership of your data.
But like any superpower, email marketing only works if you know how to use it properly. (My Gen X brethren may be hearing the theme to The Greatest American Hero play in their heads right now.) Believe it or not…most marketers are walking around right now like mere mortals when they could be swinging from the rooftops like a certain friendly neighborhood web-crawler.
Here’s what Jessica taught me about unlocking email’s true potential.
Superpower #1: True Ownership (But Only If You Earn It)
In Jessica’s own words, our subscriber base “is an owned database. Nobody can take this from us, which is really one of email’s big superpowers.”
While Instagram can go down during your big sale (and it will), and TikTok can get shut down by the US government, your email list keeps working. But Jessica was quick to point out that ownership comes with serious responsibility.
If your open rates dropped from 20-30% to 5% over the past year, Jessica says you’re probably missing DMARC—the third type of email authentication that Google and Yahoo now essentially require. “A lot of people think if I sent it and it doesn’t bounce back to me as undeliverable, then it delivered,” she explained. “That’s just not true.”
The bigger lesson Jessica hammered home? Permission isn’t optional anymore. “It takes a couple of clicks on the spam button for us to actually kind of look like spam. 0.1% of our list calls us spam, and Google Suite and Yahoo and Outlook all kind of think we’re spam.”
That’s not a typo—less than one-tenth of one percent can torpedo your deliverability. Jessica’s golden rule is stupidly simple but incredibly powerful: “We have to do what we said we were going to do for the people that asked to receive it.”
Superpower #2: Perfect Timing Through Automation
Automation is one of email’s superpowers, but that doesn’t require a complex, 15-step automation sequence.
“One of the most powerful automated campaigns in your arsenal if you’re B2B is that lead nurture campaign,” Jessica told me. “On the B2C side, we call it a welcome email.” Whether you’re B2B or B2C, this is when people are most engaged with your brand.
Jessica’s approach is simple: a three-email welcome series. The first email delivers on whatever you promised (discount, download, etc.). The second goes deeper—what were they looking for, and how can you help them take the next step? The third is like a “you-may-also-like” algorithm, introducing them to other valuable content or services.
“You’re never going to get more engagement with them than in the first few emails that you send,” Jessica explained. Most businesses waste this opportunity with a polite handshake or generic welcome message when they should be building a relationship.
Superpower #3: Behavioral Triggers That Actually Work
Another thing that might be limiting your power set? Focusing on demographics when you should have been watching behaviors.
For e-commerce, abandoned cart emails are obvious. But Jessica’s insight was deeper: “You have gotten all the way to putting my item in your cart. I know you want it. Something made you not buy. What is it?”
The sequence shouldn’t just remind people they forgot something—it should address why they left. Free shipping offer? Customer testimonials? Easy returns? “The behaviors of e-commerce are so trackable, deliciously, deliciously trackable,” Jessica said with the enthusiasm of someone who genuinely loves data.
For B2B companies, Jessica pointed to something most people forget: referral campaigns. “Once you know they’re happy, ask them for the introduction to somebody else that could use you. Especially in SaaS, there is nothing like the truth spoken by somebody who’s like you.”
Superpower #4: The Birthday Campaign Goldmine
If you’re in B2C, Jessica has a proven tactic at the ready: “If you have any excuse at all to run a birthday campaign, it will drive more revenue than almost any other campaign you do, maybe more than any other campaign you do.”
People expect to be celebrated on their birthday. They’re more likely to treat themselves. They’re more forgiving of promotional content. As Jessica put it, it’s your guaranteed audience of people already in a buying mood.
The key is making it feel genuine. Not just “Happy birthday! Here’s 20% off” but “We’re celebrating you today” with a thoughtful offer that fits your brand.
Superpower #5: Seeing Through the Open Rate Lie
Jessica delivered some hard truth about metrics: “Opens are a lie. I mean, opens were always kind of a lie. But since iOS 15, and this has now been almost four years ago, all of our open rates have magically gone up by 50%.”
Apple devices pre-load email images even if someone never opens the email, which means open rate data is about as reliable as a weather forecast for next month. Jessica’s advice? “Look beyond the open, not just to the click, but to what happens after the click.”
She walked me through using UTM parameters to track which emails actually drive website conversions. That’s where the real insights live—not in vanity metrics, but in actual business results.
The Kryptonite: Dead Weight Subscribers
Even email superpowers have weaknesses. Jessica explained that thousands of unengaged subscribers aren’t neutral—they’re actively hurting your deliverability.
“A list of people that’s sleeping on you looks bad,” she said. “If you have a low open rate because you’ve got a bunch of dead weight in your list, it looks like you’re not a very engaging sender.”
Her solution? A three-email re-engagement campaign asking people if they want to stay or go. “If you can’t reengage them, it’s time to move them along,” Jessica advised. “They don’t belong in your email list anymore.”
ROI Over Best Practices Every Time
This might have been Jessica’s most valuable insight. The industry preaches endless segmentation and personalization, but Jessica cuts through the noise: “If it doesn’t pay us back, I wouldn’t do it. If it does not pay me back for my time spent doing it, I’m not going to do it. And I’m not going to let you do it either.”
She gave a perfect example: “Three segments, I can almost always see the ROI. A 15-segment email campaign is going to take me a week and a half to do, and I’m going to basically have to start my next email campaign the next day. It’s just not going to pay me back.”
Jessica’s Quarterly Reality Check
One practice Jessica swears by is looking at your top and worst performers quarterly (or at least annually). “You will inevitably learn something you didn’t realize was happening,” she promised.
Maybe emails with video consistently get five times more clicks. Maybe Wednesday sends outperform Monday sends by 40%. Maybe your “editorial” content drives more conversions than your promotional stuff. These patterns become the foundation for testing what actually works for your business.
The Action Plan Jessica Would Approve
Based on everything Jessica taught me, here’s what every business should do immediately:
- Fix your authentication—Get DMARC configured alongside your existing SPF and DKIM
- Build a three-email welcome series—Deliver value immediately, then deepen the relationship
- Set up behavioral triggers—Abandoned cart, birthday campaigns, or referral requests based on your business model
- Track real conversions—Use UTM parameters to see which emails drive actual business results
- Clean house annually—Remove unengaged subscribers with a re-engagement campaign
- Focus on ROI—Test what matters, implement what pays, skip what doesn’t
Why This Matters More Than Ever
In a world where social platforms can disappear or become irrelevant overnight and ad costs can skyrocket without warning, your email list is the one marketing asset nobody can take away from you. But like Jessica showed me, it only works if you treat it with the respect it deserves.
The bottom line is that your email list isn’t just another marketing channel—it’s your direct line to the people who matter most to your business. Time to start treating it like the superpower Jessica knows it can be.
Flex Your Email Marketing Superpowers Episode Transcript
Rich: My next guest has over 15 years of experience in email marketing, CRM, and permission-based, data-driven marketing. She’s helped clients drive revenue from customer data in industries such as restaurant and hospitality, travel, retail, e-commerce, nonprofit universities, and more. She’s taught marketers from New York City to Barcelona, from Vancouver to Dublin, and even at SXSW Interactive in Austin.
She’s the owner and chief strategist of BetterAve, a consultancy focused on implementing the marketing best practices and MarTech harmony she preaches on stage for her clients. Today we’re going to be talking about unlocking your email marketing’s superpowers with Jessica Best. Jessica, hello, welcome to the podcast.
Jessica: Thanks for having me.
Rich: It’s exciting. Alright, since we’re talking superpowers, let’s talk origin stories. As a little girl, while other kids were playing with Legos or creating pillow forts, were you building out elegant email drip campaigns, or did the email marketing thing happen later in life?
Jessica: Admittedly, I am old enough that email, even between human beings, did not exist when I was growing up. So my origin story had to start with a different kind of nerdy thing. I was certainly a ‘skin my knees, don’t come home till it’s dark out’ type of kid. But I was also a, if you put a bowl of quarters in front of me, I will count and roll all of them.
So I’ve always liked how numbers work in my brain. I’ve liked the ability to sort of count things or track things or understand how things work. So I was an early nerd, I guess. But no, email marketing had to come later in life because it simply did not exist when I was younger.
Rich: So if you put a role of quarters in front of me, and this is where I thought you were going, I would’ve gone down to the local bowling alley in Needham, MA and just spent it all on Donkey Kong Jr. So there you go.
Jessica: Oh no. What I would do is I liked the counting of it. I liked the quantification of it. And then I would immediately take it to the Osco Drugstore and just buy however many Snickers bars a roll of quarters gets you.
Rich: Very good. All right.
Jessica: On top of everything, so.
Rich: Now after seeing you present at Content Jam earlier this year, I know you are an email evangelist. Why do you feel that email marketing is such a powerful channel for businesses today? Especially because we have other channels like social media and paid ads, and of course our websites.
Jessica: We do have all those things, and they all have their value. We can’t do anything without any one of those ingredients. Some days we do have to go without one or two of them, right? We’ve had some days, in my larger agency days, I remember the days when Instagram is down. It’s a bad day because there’s no way to replace that revenue. We’re talking about paid media on Instagram. If I go a day without spending money on Instagram, there’s in some cases hundreds of thousands of dollars of revenue lost for that.
And that’s really one of the big, I think, benefits of email as a partner for social media and paid media and just even our website. This is an owned database. Nobody can take this from us, which is really one of email’s big superpowers. This is first party data, and we’re in a very post-privacy apocalypse. Like you’re talking origin story. I realized that I got to keep control of my results and my relationships with email marketing.
Maybe social media goes, maybe TikTok goes down for the weekend. That’s never happened before. That’s really hard to replace. You can’t pick up your TikTok followers and take them anywhere else that’s owned information for that platform. Websites are an absolute bedrock ingredient in our marketing mix, but it doesn’t inherently drive any action to it. It needs the support of these other channels to drive action to it.
Email’s place in that mix is that we are owned data from people who have given it willingly, that are interested in what we have, maybe qualified for what we need, what we serve or sell, and they’ve agreed to be nudged along the funnel to go back to our website, to have a phone call with our sales rep, to put things in our cart, those types of things. So email’s really that… what’s the assist player? You get the most assists in a game… MVP player, but on assists.
Rich: Right, there you go. Yeah. Whatever that sport ball is, it plays whatever the sports ball is.
Jessica: I know we’re in the NBA playoffs. That’s the best I can do.
Rich: See, my team’s already out, so I’ve already shut that part of my brain off. But I hear, I understand what you’re saying.
So it sounds like you’ve had a lot of these conversations before about how important to email marketing is. So I’m just curious about what are the problems that people brought to you? What are some of the most common misconceptions that business owners and marketers have about email today?
Jessica: So one of them, one of the biggest misconceptions is also one of the biggest questions I’ve gotten for the last six months. Deliverability. Ooh, that’s a lot of syllables. What does that mean? A lot of people think if I sent it and it doesn’t bounce back to me as undeliverable, then it delivered. And a lot of email platforms, unfortunately, use that same terminology for the word ‘delivered’, which is not actually right. Just because it didn’t bounce back doesn’t mean that it went to somebody’s inbox. There’s the junk folder and then there’s this whole missing option. They don’t have to even put you in the junk folder if they really think you’re bad.
So there’s this misconception that email is a send and it goes type of channel. And that’s just not true. So a lot of what I’ve heard in the last six months has actually been folks reaching out to me saying, “We used to get 20%-30% open rates, we’re down to 5% open rates. Any idea what’s going on?” I do have an idea what’s going on.
Hey, did you read anything last year about how Google and Yahoo are requiring this third type of authentication that you probably didn’t know there were two other types of authentication? Because when you set up your email platform, your email platform took care of this in a two-step call and you didn’t remember doing it. There’s a new one now, and as of February of last year, if you don’t have that, you probably did have some missteps, right? You probably realized, oh, I don’t know that we’re actually hitting inbox is the way that we thought. And so I’ve had a lot of inbound questions about inbox placement, aka deliverability, and how we got here and how we get out of here.
And I’ll just answer that really quickly for anyone listening that’s like, oh, that’s so interesting. That’s my problem. That’s so interesting. Two things. One, making sure that you’re authenticated with all three types of authentication. And you could just Google “email authentication” and DMARC is the thing that will show up for the last year.
But two, it really is about getting the permission of the people who are on your list, and sending them the value that you promised them. That’s it. If I get no more words for the rest of the pod, that’s the value of email marketing is we have to do what we said we were going to do for the people that asked to receive it.
If somebody doesn’t want our email or doesn’t want our email anymore, or thinks they didn’t sign up for our email, it takes a couple of clicks on the spam button for us to actually look like spam. 0.1% of our list calls us spam, and Google Suite and Yahoo and Outlook all kind of think we’re spam. So permission is the name of the game. We’re really trying to make sure that we deliver what we said we were going to, to people that asked for it.
Rich: So just to recap that, there are now three types of authentication. The most recent one is called DMARC. If people have noticed that their email delivery deliverability or open rates have gone down, and they are still at least in their own opinion, sending out high quality, valuable content to their ideal customers, then check your DMARC for sure. That would be one of the first things. And then if that’s all set, then maybe you should question whether you are delivering value to the people who have subscribed.
Now you’ve stated that one of email’s superpowers is email automation. So what is email automation as you see it? And then what do you think is the must have email automation that any small business or even a solopreneur should get started with?
Jessica: Automation is one of emails maybe two superpowers. Data in general, I think is… so on the front end permission, we have a first party database, we have a relationship with these people. That’s irreplaceable. Great. Got it. Check. Now it’s about how do we use data because every single email that we send can be customized or sent at a different time based on what that relationship with that person is.
Let’s say you just filled out a lead form on my website. One of the most powerful automated campaigns in your arsenal, if you’re B2B, is that lead nurture campaign. On the B2C side, we call it a welcome email. You signed up for my newsletter and I sent you a welcome email, right? You should do that.
But B2B, that’s a whole different, you’re at a different superpower, right? Because that person has literally said, “I have questions I think you have the answers to.” That should dial in a response from you. You should have a salesperson call them or respond to them. You should warm them up with a lead nurture series to get them down the funnel. Maybe it’s time for a demo. Maybe it’s time for a conversation. Maybe I can help with pricing. That is the non-negotiable low hanging fruit for B2B email marketing. You could literally not do your newsletter and just do lead nurture, and I would give you a point, that’s how important it is.
On the B2C side, and even if you’re a small business, consumer goods, local store, those types of things, restaurants, they really need the welcome email. And I will put an asterisk next to that because I think a lot of people do the welcome email, great, you’re in, and that’s it. Just like a good lead nurture, here’s probably more that than that we can say.
And so welcome series going up to a series of three emails where the first one is, “here’s what you signed up for and here’s the value that I promised you”, whether it’s free dessert at a restaurant, a free download, whatever it is. And then the second email can go a little bit further. “What is it that you were looking for?” Can we help you start your order for an online restaurant or help you start shopping or whatever. Versus, do you have any questions about the service offering that we provide?, and starting that conversation. Remember, email is two-way. If somebody replies back, that’s actually a good thing.
And then the third one might be, you may also like algorithm, right? You sign up for a reason, here’s other stuff you might like. And that could be “find us in social media”. Might as well give a tip of the hat to the social media channels while we’re in here. It could be you downloaded this white paper here, or two more pieces of primary research that we put together that you might find interesting. All of that deepens and strengthens the relationship with this brand-new subscriber, because you’re never going to get more engagement with them than in the first few emails that you send.
Rich: So from what I heard, if they’re basically the same thing, if you’re on the B2B side, you might call it a lead nurturing campaign. Sounds more expensive. On the B2C side, basically it’s a welcome message, but they both serve the same purpose.
This is a time when clients or prospects are most engaged with our content. They’re most interested in what we have to say. They’re most likely to remember us, because hopefully they just signed up for our email newsletter. And so we need to have a series of things that kind of starts to build the trust in that relationship. Is that pretty much what we’re looking for?
Jessica: Exactly. We’re going to start delivering on the value that we promised them immediately. Why did they sign up? 10% discount, free research, register for a webinar. Whatever it was, we’re going to start delivering on the value that we promised them right away.
Rich: Alright. And then so that’s triggered by somebody, I assume, signing up or downloading whatever it is that we ask them to do.
What is another, or maybe a couple of other automations, whether it’s an e-commerce site or it’s a lead gen site, that maybe is the next step up, the next thing that we should tackle?
Jessica: And I love that you gave me the range. Because it’s so different. What’s the next best email you can send? Are you a $20 billion SaaS B2B company. Are you a widgets e-commerce company? Are you a restaurant that’s got two locations? That very much depends on the next thing for restaurants.
The second, maybe the first most revenue driving campaign you can do is your birthday campaign. If you are a consumer facing brand that has any excuse at all to wish somebody happy birthday, “celebrate with us, we’ll buy you a piece of cake”. “Happy birthday from us, we’ll give you a 15% discount on your favorite pair of pants”, whatever it is. If you have any excuse at all to run a birthday campaign, it will drive more revenue than almost any other campaign you do. Maybe more than any other campaign you do.
If you are a B2B large, I want to stick with large B2B SaaS company, and you get somebody through the nurture series, through onboarding, lots of opportunities for automation along the way, right? I’m just shopping. I’m trying to decide between you and somebody else I’ve onboarded. I have lots of questions. All of those are great points for automation, but here’s the one that most people forget at the other end of the funnel. The collection bucket.
You’ve got clients and customers and you know that they’re happy because of course you’re triggering NPS surveys or customer satisfaction surveys to them. Once you know they’re happy, ask them for the introduction to somebody else that could use you. Especially in SaaS, there is nothing like the truth spoken by somebody who’s like you, who knows that this is not just a bad piece of software. So in SaaS, I would say it’s referral. Don’t forget going all the way to the end of the journey and asking for that referral to fill the top of the funnel.
And then the last sort of spot in the journey, I think there’s a lot, if you map out your customer’s journey you’ll start to see those moments really easily. But the one that most people think of in e-commerce is abandoned cart. You have gotten all the way to putting my item in your cart. I know you want it. Something made you not buy. What is it? Is it you got distracted and you just need a reminder, no discount? Or do you need a free shipping offer?
So there’s usually a moment in the e-commerce. The behaviors of e-comm are so deliciously trackable. That’s a moment that we can monitor and say that is a really close lead. I know I can close that person.
Rich: So we’ve talked a little bit about some of these automations, and then there’s also sending out regular emails. So if we are now sending out regular emails, how do we make sure that we’re not just going through the motions because we were told email marketing is important? How do we make sure that we’re being purposeful with our email marketing and that it’s supporting the rest of our business?
Jessica: I think email marketing is lovely, partially because it’s fast and easy to do. But I do think that sometimes we can go, okay, I got to get an email out the door, and then I’ve got 17 other things on my list of things to do. It’s somewhat easy just to go check, I know exactly how to do it, I’m going to build it and it’s going to go out and it’s going to be great.
One of my favorite checks is whether it’s quarterly, monthly, annually. If you can’t do it more often than that, take a look at your top performers. You will inevitably learn something you didn’t realize was happening. There’s some trend or pattern or best performer or worst performer in that list that you can start to say, oh, maybe I should actually A/B split test that to see if it is true that when I do it this way, it lifts, and when I do it this way, it detracts from my results.
Again, if one thing that I get you to do extra above and beyond sending email, especially if you’ve got regular content going out the door, you’ve got some of these automated emails that turned on a year ago and you maybe haven’t checked on once a quarter. If you can do it, take a look back at your results for the last year and see what your top and under performers are and what do they have in common. What can you learn from that and what can you start to test and prove against that learning?
Rich: So it’s always a challenge with small businesses, because we don’t have as much data points as these giant corporations or these SaaS companies. So let’s say I go back, and I look at 12 months of email newsletters and maybe 12 of them went out, maybe 24 of them went out. Maybe I’m really productive and I got a whole 52 out there.
But if I look at these and I see, okay, we have a couple of ones at higher open rates or higher click-through rates, a couple that didn’t, how do I know? What is the real answer here? Is it because I sent them out at a different time of day? Is it because I used an emoji in the subject line? Is it because I got a really high open rate and a low click through rate? Because really I gave all the information away in the email itself, so nobody had to visit my website.
Like sometimes I feel okay, I know that’s the right thing to do. But I’m not sure how to interpret that information in a way that it’s useful or that I can take action on it.
Jessica: Yeah, and I’ll tell you, it’s even harder now because opens are a lie. I mean, opens are always kind of a lie. But since iOS 15, and this has now been almost four years ago, all of our open rates have magically gone up by 50%. So we’re all smarter, we’re all better at our jobs than we were three years ago. I hope that’s true, but it’s not because our open rates have not gotten better because we’re suddenly magically doing better stuff.
iOS 15 on iPhone and Apple devices is pre-opening our emails by loading the images, even if somebody never actually opens the email. So that’s throwing some of our data off. So now you’re looking at these results for the last 12 months and you’re like, “Oh, a 50% open rate. I never got one of those before”. What you’re comparing to also needs to be in the last 12 months, I would say. If you’re looking at something compared to four years ago, everything this year is going to win. That’s just how numbers look.
So use open rate sparingly, I guess. You are probably more interested, and this also answers your question of what’s working, what are people interested in, what’s actually getting engagement? Look beyond the open, not just to the click, but to what happens after the click.
Again, small company, maybe you have three articles in your newsletter every week, or you have three products featured in your newsletter every week, whatever it is. What’s actually getting clicks? Is it always something in the top spot that tends to get higher clicks? But is there anything that ran away with it? There’s a video in the third spot that just got five times as many clicks as the other sections in the email. I happen to know that video does drive up engagement, that video does more often get clicks on it. So I would use that as a learning tool. I would go test that and see if I use a video versus don’t use a video.
Or, one step beyond the click. If you’re using Google Analytics, UTM tags on your links. Again, you can Google UTM tags and you can learn more than you ever wanted to know. But basically, we’re adding a string of characters to the end of our links that doesn’t change where the person goes. It just makes sure that Google Analytics knows that this person came from an email campaign and which campaign they came from. So the magic of that is now that somebody’s on the site again, B2B or form fill for the website for any reason, I can see that form fill was because of this email campaign. Now I’m really onto something, right?
A perfect example of this was Delta Faucet. When I was working with Delta Faucet, they don’t actually sell a lot of faucets on their websites. You have to go to Home Depot or Lowe’s. But they had a “where to buy” link on the page. The emails had been editorial for the whole year. They were like, yeah, it’s a style newsletter. And I was like, totally get it. Totally get it. Editorial, got it. They refused to put featured products in their newsletter. And I was like, okay, but then what are we doing here? Let’s just try it.
And lo and behold, when we tested it or just tried it, we actually split test this one. And when we added a product to the email, those emails consistently drove three, four times as many “where to buy” clicks on the website as editorial content did, because we’re showing you the product that we want you to buy. So those are the types of things. I love a good editorial newsletter just like everybody else, but we had to learn our way. We had to prove that by actually showing products in an editorial newsletter, we could both be style and function.
So clicks, website conversions over open rates, that should get you pretty close to what you think might be working. I will say again, open rate can be good comparatively. So if you get like a 60% open rate on one of your emails and your usual is 30 in the last 12 months, something about that subject line or that headline probably worked.
But to your point, if we got a 60% open rate, but half our normal click through rate, it didn’t follow through. Something didn’t grab them. Or we put everything in the email, which for some brands is just okay. If you have 18-month sales cycle, don’t be afraid of making a newsletter where people get everything they need just by reading the newsletter. That’s not bad.
Rich: All right. So to get those clicks and to get that traffic to the website, get people to take action. Obviously, they need to open up that email in the first place, and so often it does come down to that subject line. Do you have any go-to hacks for crafting engaging subject lines that get people to open up emails?
Jessica: So two things to that. First, did you know that 40% of why somebody opens your email is the subject line? 40% of why somebody opens your email is the from name. So be careful with your from name. I think for a while it was very popular, especially in B2B, to sign emails or send emails from the sales rep that’s calling. But if you don’t know Stacy in sales, then you just got an email from an unknown person. And in a really full inbox, that can get lost very fast.
So be careful with sending from a person until there’s an established relationship with that person. Or if you have a celebrity CEO or something, go nuts. But most of us don’t know the staff. At the brands that we’re subscribed to. So we want to be really careful with that. So ‘from’ name is just as important as subject line, if you can believe it.
And then there’s another piece that to be written with the subject line that shows up as preview text in the inbox called “preheader text”. So everyone might write a really good subject line, then forget that you have this additional, it’s actually two lines on an iPhone. You get one line for subject line and two lines of preview text. Don’t forget to fill your pre-header text with something that supports that open or that subject line to drive that open.
So that was not what you asked me, but I wanted to give you that context. Because I feel like sometimes people get really concerned about their subject line and they forget that there are these two other really important factors showing up in the inbox.
As for subject line, I don’t believe in hacks, I believe in tests. I believe that we can test marketing mechanisms to understand whether curiosity, mystery, the curiosity gap that Drew Davis talks about versus value, a discount. If you have a discount in your email, you don’t test it. I’m telling you, don’t test it. If you have an offer in your email, you have to put it in the subject line, not in the pre-header. In the subject line. That usually wins, and the word ‘free’, and the word ‘you’. We know like chemically, our brains are so tuned into those words. Those are the marketing mechanisms that we think are going to be the most effective in the subject line when they’re relevant.
I would back that up with a level two and just say first name is another great brain code sheet. Like you’re required to see your name and write. I don’t know what that is, but we’re very trained to see our own name and any other relevant information. Because I live in Kansas City, when ‘Kansas City’ is in the subject line, that one also makes my skin tingle a little, right? I also sit up a little bit straighter and take notice of that. Relevance, I think, is another really good key to a great subject line.
Rich: Alright. Now let’s talk maybe about the end of the email chain here. Which is, if your list has thousands of unengaged subscribers, from what I’ve learned this year, is that can actually hurt your deliverability rate if they’re just not opening, not doing anything with it. So how do you recommend we re-engage them? Or do we just cut them loose?
Jessica: Yes. Both.
Rich: Okay.
Jessica: So first we’re going to try to reengage them because that is our right to do. We are probably going to start with a re-engagement campaign of three emails, sending one email to a bunch of people who haven’t opened an email in a year. It’s medium effective. But if we make the subject line really clear and we set up a series of three emails, “Do you want to set your preferences?” “Are you still interested?” “This is goodbye”.
Send that series and then, I don’t know, 1%, 2% will say, yeah, I’ll stay. Another 2% might literally unsubscribe. 95% of your list is going to take no action because that’s what they’ve been doing for the last year. And I would argue for that exact reason, deliverability is very complicated. There’s a lot that goes into it. It’s not just authentication and permission, although that is a great place to start. A list of people that’s sleeping on you looks bad, right?
If you have a low open rate because you’ve got a bunch of dead weight in your list, it looks like you’re not a very engaging sender. And so that can actually impact whether the awake half of your audience gets your emails. So I would say in light of all of that, I would say if you can’t reengage them, it’s time to move them along. You can keep them in a sales CRM if you’re B2B, but they don’t belong in your email list anymore. They’re not even there probably.
Rich: How would you handle it? So we send out these three emails.
Jessica: Yes.
Rich: Asking for a friend. So we send out these three emails, and each one gives the, “do you want to stay or do you want to go?” And then the “do you want to go button?” basically unsubscribes them immediately. If you want to stay, that automatically resubscribe them.
But that audience that has opened one of those, do you see an open as a sign of engagement and we keep them, we take them off the sleepy list? Or do you feel that they have to take that action to click on that link?
And to make it an even more complicated question, what if we say that the first time we try and clean our list, we make it open rates. Oh, if they open it, they stay. But if we do this again, opening an email is not enough. Thoughts on that one, Jessica?
Jessica: Fair question from your friend. I appreciate your friend today.
Rich: Yeah, my friend has a lot of email problems.
Jessica: So here’s my thing. Remember I said that opens are now a lie? So your open from somebody that if you literally get a list of people that has not opened or clicked in over a year, then even these false opens aren’t firing for some reason. If something happens during this re-engagement campaign where you literally get an open, to me, that’s not enough. I need a human being to take an action on the other side of that in order to keep that person on my list.
Because mostly when we’re doing a reengagement campaign, our goal at the end of the reengagement campaign is a better list. And an open right now really isn’t synonymous with action. So I would say, I get brave, and I would say those people that have opened but not clicked, maybe they deserve – it depends on if you’re a small enough list that you can do this – maybe they deserve a personal outreach from your friend that says, “Hey, I noticed that you got this email. Before we take you off the list, I just want to make sure that you’re okay without our emails” or whatever. And if they don’t respond to you either, let them go. They got to go.
Rich: Sounds good. All right. I’ll tell my friend. All right, let’s see. So we’ve talked about a lot of different things today. I want to know about KPIs. What are the things that you recommend as marketers we pay attention to, strictly from this channel? So if we’re trying to determine how effective, how much money and time we should be putting towards email marketing, what are the KPIs we should be attuned to?
Jessica: Great question. I think we start with things that we can track in email, like clicks. This got more clicks versus this thing, that’s a good, before I even leave the platform I know if I’m on the right track. I hate stopping there. Whether it’s e-commerce, bless our faces, e-commerce people, you go on to track revenue and watch it rain money. For the rest of us that have an offline sale or have a long tail sale, that isn’t going to happen in the next click. Those are harder.
But it is totally worth it to do either match back attribution, like this person got an email and then within 30 days, they bought a vehicle. Whatever it is, doing that match back attribution is probably worth it, at least in an annual report or some big moment where we’re doing attribution. And the reason for that is I believe strongly that while all of these things can be good indicators, if it doesn’t make us money, we shouldn’t spend our time or our money on it.
Email is actually extremely cost effective and it’s almost hard to spend more money in email to make more money, because it’s this sort of one database. Unless the biggest way we can grow our email revenue is by growing our database, but it’s harder to juice that lemon over and over again just by sending more often. It doesn’t often get us huge returns. And so for me, I’m looking for something with a high conversion rate or high conversions. And I say both, because the best conversion rate you get is going to be to like 20 people in your database, and you had three people convert and you’re like, yeah, I did good conversion rate. Not a scalable way to run a business.
So there’s going to have to be a combination of how do you get a great conversion rate through all of the parts of your list, whether that’s the engaged portion, the unengaged portion, the heavy buyer, the top buyers, whatever that is. You’re looking for something that increases the conversion rate per segment of your list so that ultimately you can increase the number of conversions from your entire email list.
For me, the name of the game is always conversions. And we can talk about that in terms of ROI. Because again, I think we can spend extra hours sometimes doing things where we’re like, yeah, I’m going to get 15 segments going. I got to tell you, I haven’t had a lot of 15 segment email campaigns that have paid me back for the amount of hours and effort that took me to create. So I would say conversions or conversion rate in tandem is probably my combo. What do you use on flyte and your clients?
Rich: We check things like, are we growing in the right direction? Are we going as fast? How many new subscribers do we have? I used to care about unsubscribes, but these days, I think unsubscribes often happen through attrition more than anything else. And then ultimately, it’s did somebody reply to an email and we started a conversation.
So yes, those are some of the ones, but I could be definitely more strategic about some of these KPIs. And after seeing you speak at Content Jam this year, Izzy and I came back to the office much more energized about our content and email marketing for both ourselves and our clients. It’s part pf the reason I wanted you to come back on the show.
Jessica: I love the list growth one. I’ll give you a pair. So I don’t super care about unsubscribes unless that the piece of it that I will watch, if it feels out of whack is if the percent of our list that’s unsubscribing or attriting is larger than my list growth.
So if I’m net negative in list growth, my list is actually shrinking, because I’m just not filling it up as fast or faster than I’m losing people from my list. That one can be a bad sign, right? We want to make sure that we’re investing.
One of the places you can actually spend cash on your email campaign is figuring out how to grow your list, whether that’s paid media, a register to win campaign, hosting a webinar, sponsoring emails, whatever that is. A lot of that can be where you spend cash money to invest in your email program. And if we feel like we’re losing more than we’re gaining, it may be that we’ve lost a little runway, a little clout, and so it’s time for us to probably pay attention to filling that back up again.
Rich: With the one caveat that if you did run some sort of exit strategy for getting dead weight off of your website or off your email list, then probably don’t worry about that list of people and just compare it with the natural ebb and flow of people joining and leaving your list.
Jessica: Agree. And I’ll tell you, about a third of your list is going to turn over every year from attrition. So don’t be afraid of that ugly, unengaged number. The good news is that your open rate is so much better than you think it is.
Rich: Good to know.
Jessica: Like if you can focus on the silver lining of an unengagement campaign, you’re right that worrying about taking those people off of your list, even if you just do it as a once a year annual campaign, shouldn’t give you any sweat.
Rich: All right. Now you signed up not just for the Agents of Change newsletter, Jessica, but also for the flyte new media newsletter. I have thick skin and my therapist is on call. What was your favorite and least favorite things about the whole onboarding process from one or both of those two email newsletters you signed up for?
Jessica: Oh, man. I think both had really good tone, so I love that the personality that you have on both sides, both brands, really came through. It felt very conversational. It felt written by you or someone who was trying to.
Rich: It really was. Yeah.
Jessica: Yeah. So I think that’s really powerful. I think in a sea of newsletters in my inbox, it was really fun to get something fun. So that was probably a highlight. I also love that you have a full onboarding series, right? There’s not just a one and done. I’m going to warm you up. It was very well spaced.
My biggest pet peeve, and this is such a, I’m not sure I can even prove that it gives you less results, but I feel like every second that we don’t send an immediate welcome email is a wasted second. And both sent immediate welcome emails. So I love that. Least favorite, I don’t know.
Rich: You can put me on the spot. I know that because of you, we uncovered the fact that we never shut off our old welcome sequence for flyte.
Jessica: No, I wasn’t going to out you, but I was like, I think the only problem I found was that I actually got two “Welcome” emails.
Rich: So we shut that off. Yeah.
Jessica: I was like, I think I got two today. And you were like, oh, okay. That’s not off.
Rich: Yeah. That this is the problem with email marketing is you don’t see it every day. So it’s every six months or a year, you should probably unsubscribe and subscribe for your own newsletter.
Jessica: Yeah. Or just go look at it if you sign up with a brand-new email address. So Google Suite has this great thing where you can use your email address plus anything you want at your domain. So you can make up as many faux email addresses as you want. Every year, go sign up with a new email address and see if it onboards you. But you’re going to have to remember to unsubscribe yourself or you’re going to get two copies of your newsletter forever.
Rich: I probably get five already. But it is important because a lot of times your services change and the way that you talk about yourself changes. So I do think that it’s a good process to go through. Agents of change can’t just go along with everything that everybody says.
So what is one popular belief in email marketing that you think is completely boneheaded or vice versa? What is something that everybody says is terrible, and in your heart of hearts is actually brilliant.
Jessica: Oh, man. Okay. I have an answer for each side, which is cheating. But the thing that everybody says is terrible, like every human being is like, I hate popups. They work so well. They do. Everyone hates them, but everyone fills it out. Tread lightly. Try and do it in a respectful way. Let somebody get halfway down the page first. Do a slide out instead of a popover or whatever. There’s lots of right ways to do it. But that’s the one that I still hear, and I’m like, it literally quadrupled my list growth. So I don’t know what to tell you.
And then I would say on the flip side, gosh. So we used to say, test everything. Like in the email industry we’re like, it’s not an email blast. We send targeted relevant email campaigns. They don’t blast everybody. We got so defensive about the terminology, but what we meant was we’re always going to segment, we’re always going to test, we’re always going to personalize whatever, using data in every campaign. And I do like those things.
I just spent half an hour talking about those things. But if it doesn’t pay us back, I wouldn’t do it. I’m not going to do it just because it’s a good idea or it’s a best practice, or because the best brands in the world do it. If it does not pay me back for my time spent doing it, I’m not going to do it and I’m not going to let you do it either. If it pays us back, like that’s why I say three segments. I can almost always see the ROI, right?
There’s a segment that’s bought burgers, there’s a segment that’s bought wings, and there’s a segment I don’t know anything about. And 80% of the sales came from the two segments I knew something about. I can see it. I can see the ROI. A 15-segment email campaign is going to take me a week and a half to do, and I’m going to basically have to start my next email campaign the next day, right? It’s just not going to pay me back. And so I stand firmly in that idea that ROI has to be there. Return on effort or return on investment has to be there in order for me to even do the base level best practices.
Rich: All right. Jessica, if somebody wants to learn more about you and BetterAve, where can we send them online?
Jessica: I’m pretty active on LinkedIn, actually. I killed Facebook and Twitter, none of that made me happy. But LinkedIn @JessicaBest, or you can find me at jessica.best. I bought the domain the day it came out. Or my company better-ave.com. And I’m pretty responsive on all three. Find me, I’ll see out there.
Rich: Excellent. And we’ll have those links in the show notes. Jessica, always a pleasure. Thank you so much for coming by today.
Jessica: Thanks for having me.
Show Notes:
Jessica Best is a data-driven marketing strategist and speaker who helps brands turn email marketing into a high-performing revenue engine. As the founder of BetterAve and a seasoned consultant, she’s worked with companies of all sizes to craft campaigns that are both smart and customer-focused.
Rich Brooks is the President of flyte new media, a web design & digital marketing agency in Portland, Maine, and founder of the Agents of Change. He’s passionate about helping small businesses grow online and has put his 25+ years of experience into the book, The Lead Machine: The Small Business Guide to Digital Marketing.